Pineapple Upside Down Sticky Buns

These Pineapple Upside Down Sticky Buns are filled with pineapple and brown sugar sticky goodness…with a cherry on top.

Pineapple Upside Down Sticky Buns

For the last three days I have been gifted rainy cooler weather.

Which I am clinging to because it’s supposed to be in the 90’s next week and that is unseasonably warm weather for around here.

But the cooler weather means I was maximizing my baking days.

And what better on a cool rainy day than a nice gooey sticky bun.

These Pineapple Upside Down Sticky Buns to be exact.

Pineapple Upside Down Sticky Buns

I love pineapple upside down cake.

So much so that I love making it in bread pudding form.

In French toast form.

And now in bun form.

There is also, of course, a pineapple upside down cake with a big twist in my cookbook.

I’m not sure why I never thought of this before.

Anything upside down is great for sticky buns since they have to bake…upside down.

Pineapple Upside Down Sticky Buns

I thought about using pineapple rings but the crushed pineapple works so much better.

It makes it so you get pineapple in every bite.

It also almost becomes candy like baking in all that sticky brown sugar goodness.

You do want to make sure that you drain and then squeeze out the extra juice from the pineapple.

I do this in a paper towel. If your pineapple is too wet it will mess with the texture of the sticky bun.

This recipe also uses pineapple juice powder which is freeze dried pineapple made into powder.

I buy it in large quantities not only for baking but it’s great in smoothies.

Pineapple Upside Down Sticky Buns

Want More Pineapple Recipes?

Pineapple Upside Down Cake Ice Cream

White Chocolate Dried Pineapple Salted Macadamia Nut Cookies

Pineapple Coconut Cream Jell-O Shots

Spiced Rum Tropical Dump Cake

Pineapple Upside Down Cake Fudge

Pineapple Upside Down Sticky Buns


  • For the rolls:
  • 1/2 cup warm water, 110 – 115F
  • 1 TBSP active dry yeast (I used Red Star Yeast Platinum)
  • 1/2 cup whole fat buttermilk, at room temperature
  • 2 large eggs
  • 1/2 cup plus 1/2 tsp granulated sugar, divided
  • 1 tsp. salt
  • 1 tsp. vanilla extract
  • 6 Tbsp unsalted butter, melted and slightly cooled
  • 3 1/2 – 4 cups bread flour
  • 1 TBSP pineapple juice powder
  • For the filling:
  • 6 TBSP unsalted butter, super soft but not quite melted
  • 1 cup packed brown sugar
  • 2 TBSP pineapple juice powder
  • Pineapple Upside Down Sticky Bun Sauce:
  • 1 cup (2 sticks) unsalted butter
  • 2 1/2 cups brown sugar, tightly packed
  • 2/3 cup light corn syrup
  • 1 1/2 cups crushed pineapple, squeezed dry with paper towel
  • Pinch of salt
  • 12 maraschino cherries


  1. Using a stand mixer with the paddle attachment add the yeast, warm water, and 1/2 tsp. granulated sugar.
  2. Let rest for 5-10 minutes to proof…the batter will puff up. If it does not then your yeast is bad and rolls won’t rise so best to throw out and start again with different yeast.
  3. Add in buttermilk, eggs, 1/2 cup granulated sugar, salt, vanilla, and melted butter and mix until fully combined.
  4. Add in 2 1/2 cups of the flour and pineapple powder and mix until fully combined.
  5. Switch to a hook attachment then add another 1 cup flour. Knead mixture until combined.
  6.  Continue to knead on low speed about 5 – 6 minutes while adding a little more flour as needed to reach a soft and moist dough (Dough shouldn’t stick to the sides of the bowl but does stick to the bottom).
  7. Transfer dough to an oiled bowl, cover with plastic wrap (I find press and seal works best)  and let rise in a warm place until doubled in volume, about 1 1/2 hours.
  8. For my rolls I used a jelly roll pan. I don’t suggest this as I bubbled over…and I was going for more of an effect for photography purposes. 🙂
  9. Grease a 9-x-13-inch pan.
  10. With 20 minutes left in the rise start to make the sticky bun sauce.
  11. In a large saucepan melt the butter.
  12. Add the brown sugar, corn syrup, and salt and bring to a low boil.
  13. Remove from stove top and fold in drained pineapple.
  14. Pour the sauce into the prepared pan.
  15. You can let sit. It will start to get hard but that is fine as once baked it will get gooey again.
  16. Punch dough down.
  17. Dust a working surface lightly with flour and turn dough out onto surface.
  18. Sprinkle top of dough with a little flour then roll dough out into an 20 by 18-inch rectangle.
  19.  Spread the softened butter evenly over entire surface (hands work best).
  20. In a small mixing bowl whisk together brown sugar and pineapple powder. Sprinkle and spread brown sugar mixture evenly over butter layer (try to leave about 1/2-inch border uncovered along all edges).
  21.  Beginning on an 18-inch side tightly roll dough into a cylinder. Pinch the seam to seal (brushing a little egg white underneath helps if needed or I just use a toothpick).
  22. Cut into 12 equal portions using a large sharp knife (they should be 1 1/2-inch each).
  23. Place a maraschino cherry in the middle of each roll.
  24. Arrange rolls cherry side down, spacing evenly apart on top of the sticky bun sauce.
  25. Cover with plastic wrap loosely.
  26. Let rise in a warm place until doubled in volume, about 1 1/2 hours. Preheat oven to 350F near the last 20 minutes of rolls rising.
  27.  Bake rolls in preheated oven until centers are no longer doughy, about 25-30 minutes.
  28. Rolls and sauce will be hot but you need to flip your rolls out onto a platter or you can be on the safer side and remove with a spatula and then spoon the sauce on top.
  29. Serve immediately.
  30. If you have leftovers the sauce will harden a little just pop on a plate in the microwave for about 20-30 seconds and you will be good to go.

Pineapple Upside Down Sticky Buns

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